Gentamicin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461198

CAS#: 1403-66-3

Description: Gentamicin is a widely used antibiotic in the intensive care unit (ICU).


Price and Availability

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Gentamicin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461198
Name: Gentamicin
CAS#: 1403-66-3
Chemical Formula: C21H43N5O7
Exact Mass: 477.3162
Molecular Weight: 477.6
Elemental Analysis: C, 52.81; H, 9.08; N, 14.66; O, 23.45


Synonym: Gentamicin; Centicin; Lyramycin; Oksitselanim; Refobacin; Septigen; Uromycine;

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(((1S,2R,3S,4S,6S)-4,6-diamino-3-(((2S,3S,6S)-3-amino-6-((S)-1-(methylamino)ethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol

InChi Key: CEAZRRDELHUEMR-ZMRLYRBASA-N

InChi Code: InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9-,10-,11-,12-,13-,14+,15+,16-,17-,18-,19-,20+,21-/m0/s1

SMILES Code: N[C@H]1CC[C@@H]([C@H](C)NC)O[C@H]1O[C@@H]([C@H](C[C@@H]2N)N)[C@@H](O)[C@H]2O[C@@H]3[C@H](O)[C@H](NC)[C@@](O)(CO3)C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Burton AJ, Giguère S, Arnold RD. Pharmacokinetics, pulmonary disposition and tolerability of liposomal gentamicin and free gentamicin in foals. Equine Vet J. 2015 Jul;47(4):467-72. doi: 10.1111/evj.12309. Epub 2014 Aug 18. PubMed PMID: 24943347.

2: Hayes GM, Gibson TW, Moens NM, Monteiro B, Johnson RJ. Intra-articular pharmacokinetics of a gentamicin impregnated collagen sponge in the canine stifle: an experimental study. Vet Surg. 2014 Feb;43(2):166-73. doi: 10.1111/j.1532-950X.2014.12115.x. Epub 2014 Jan 10. PubMed PMID: 24410710.

3: Bauquier JR, Boston RC, Sweeney RW, Wilkins PA, Nolen-Walston RD. Plasma Peak and Trough Gentamicin Concentrations in Hospitalized Horses Receiving Intravenously Administered Gentamicin. J Vet Intern Med. 2015 Nov-Dec;29(6):1660-6. doi: 10.1111/jvim.13626. Epub 2015 Oct 1. PubMed PMID: 26426540; PubMed Central PMCID: PMC4895685.

4: Johnston C, Hilmer SN, McLachlan AJ, Matthews ST, Carroll PR, Kirkpatrick CM. The impact of frailty on pharmacokinetics in older people: using gentamicin population pharmacokinetic modeling to investigate changes in renal drug clearance by glomerular filtration. Eur J Clin Pharmacol. 2014 May;70(5):549-55. doi: 10.1007/s00228-014-1652-7. Epub 2014 Feb 14. PubMed PMID: 24522409.

5: Telechea H, Gesuele J, Grosso P, Galarraga F, Guzzo F, Speranza N, Antúnez F, Nanni L, Giachetto G. [Gentamicin pharmacokinetics in term newborn: ¿Is it necessary to systematically monitor plasmatic levels?]. Rev Chilena Infectol. 2016 Feb;33(1):7-11. doi: 10.4067/S0716-10182016000100001. Spanish. PubMed PMID: 26965871.

6: Imbuluzqueta E, Gamazo C, Lana H, Campanero MÁ, Salas D, Gil AG, Elizondo E, Ventosa N, Veciana J, Blanco-Prieto MJ. Hydrophobic gentamicin-loaded nanoparticles are effective against Brucella melitensis infection in mice. Antimicrob Agents Chemother. 2013 Jul;57(7):3326-33. doi: 10.1128/AAC.00378-13. Epub 2013 May 6. PubMed PMID: 23650167; PubMed Central PMCID: PMC3697350.

7: Veinstein A, Venisse N, Badin J, Pinsard M, Robert R, Dupuis A. Gentamicin in hemodialyzed critical care patients: early dialysis after administration of a high dose should be considered. Antimicrob Agents Chemother. 2013 Feb;57(2):977-82. doi: 10.1128/AAC.01762-12. Epub 2012 Dec 10. PubMed PMID: 23229487; PubMed Central PMCID: PMC3553715.

8: Webb JC, Gbejuade H, Lovering A, Spencer R. Characterisation of in vivo release of gentamicin from polymethyl methacrylate cement using a novel method. Int Orthop. 2013 Oct;37(10):2031-6. doi: 10.1007/s00264-013-1914-5. Epub 2013 May 19. PubMed PMID: 23685878; PubMed Central PMCID: PMC3779555.

9: Rankin AJ, Lanuza R, KuKanich B, Crumley WC, Pucket JD, Allbaugh RA, Meekins JM. Measurement of plasma gentamicin concentrations postchemical ciliary body ablation in dogs with chronic glaucoma. Vet Ophthalmol. 2016 Jan;19(1):57-62. doi: 10.1111/vop.12258. Epub 2015 Feb 17. PubMed PMID: 25688853.

10: Salouti M, Heidari Z, Ahangari A, Zare S. Enhanced delivery of gentamicin to infection foci due to Staphylococcus aureus using gold nanorods. Drug Deliv. 2016;23(1):49-54. doi: 10.3109/10717544.2014.903533. Epub 2014 Apr 24. PubMed PMID: 24758188.

11: Byrnes M, Dorman R. Use of Gentamicin as Empiric Coverage for Ventilator-Associated Pneumonia: The "Con" Perspective. Surg Infect (Larchmt). 2016 Jun;17(3):334-6. doi: 10.1089/sur.2015.278. Review. PubMed PMID: 27206240.

12: Ravis WR, Llanos-Cuentas A, Sosa N, Kreishman-Deitrick M, Kopydlowski KM, Nielsen C, Smith KS, Smith PL, Ransom JH, Lin YJ, Grogl M. Pharmacokinetics and absorption of paromomycin and gentamicin from topical creams used to treat cutaneous leishmaniasis. Antimicrob Agents Chemother. 2013 Oct;57(10):4809-15. doi: 10.1128/AAC.00628-13. Epub 2013 Jul 22. PubMed PMID: 23877689; PubMed Central PMCID: PMC3811440.

13: Dhuria RS, Bhatti R, Bhatti MS, Singh P, Whitcomb PJ, Thukral AK. Experimental design optimization for electrochemical removal of gentamicin: toxicity evaluation and degradation pathway. Water Sci Technol. 2013;67(9):2017-24. doi: 10.2166/wst.2013.076. PubMed PMID: 23656945.

14: Varghese JM, Roberts JA, Wallis SC, Boots RJ, Healy H, Fassett RG, Lipman J, Ranganathan D. Pharmacokinetics of intraperitoneal gentamicin in peritoneal dialysis patients with peritonitis (GIPD study). Clin J Am Soc Nephrol. 2012 Aug;7(8):1249-56. doi: 10.2215/CJN.12211211. Epub 2012 Jun 14. PubMed PMID: 22700884; PubMed Central PMCID: PMC3408127.

15: Dersch-Mills D, Akierman A, Alshaikh B, Yusuf K. Validation of a dosage individualization table for extended-interval gentamicin in neonates. Ann Pharmacother. 2012 Jul-Aug;46(7-8):935-42. doi: 10.1345/aph.1R029. Epub 2012 Jun 26. PubMed PMID: 22739714.

16: Alshaikh B, Dersch-Mills D, Taylor R, Akierman AR, Yusuf K. Extended interval dosing of gentamicin in premature neonates ≤ 28-week gestation. Acta Paediatr. 2012 Nov;101(11):1134-9. doi: 10.1111/j.1651-2227.2012.02820.x. Epub 2012 Sep 7. PubMed PMID: 22897142.

17: Rotov KA, Tikhonov SN, Alekseev VV, Snatenkov EA. Pharmacokinetics of liposomal gentamicin. Bull Exp Biol Med. 2012 Aug;153(4):475-7. English, Russian. PubMed PMID: 22977848.

18: Fullas F, Padomek MT, Thieman CJ, Van Gorp AE. Comparative evaluation of six extended-interval gentamicin dosing regimens in premature and full-term neonates. Am J Health Syst Pharm. 2011 Jan 1;68(1):52-6. doi: 10.2146/ajhp100114. PubMed PMID: 21164066.

19: Momoh MA, Esimone CO. Phospholipon 90H (P90H)-based PEGylated microscopic lipospheres delivery system for gentamicin: an antibiotic evaluation. Asian Pac J Trop Biomed. 2012 Nov;2(11):889-94. doi: 10.1016/S2221-1691(12)60248-2. PubMed PMID: 23569866; PubMed Central PMCID: PMC3609242.

20: Barth RE, Vogely HC, Hoepelman AI, Peters EJ. 'To bead or not to bead?' Treatment of osteomyelitis and prosthetic joint-associated infections with gentamicin bead chains. Int J Antimicrob Agents. 2011 Nov;38(5):371-5. doi: 10.1016/j.ijantimicag.2011.03.008. Epub 2011 May 6. Review. PubMed PMID: 21549570.